Use of organoboron compounds as antifouling agents

Abstract

There is provided a method for controlling or combatting the attachment of a fouling organism to an underwater surface which comprises contacting said organism with an antifouling-effective amount of a diarylboron compound of formula I. A method for protecting aquatic structures against fouling by a marine or freshwater fouling organism and antifoulant compositions therefor are also provided. ##STR1##

We claim: 
     
       1. A method for controlling or combatting the attachment of a fouling organism to an underwater surface which comprises contacting said organism or the locus thereof with an antifouling effective amount of a compound of formula I ##STR6## wherein R is C 1  -C 8  alkyl, C 2  -C 8  alkenyl or C 2  -C 8  alkynyl; W and Y are each independently halogen, C 1  -C 8  alkyl or C 1  -C 8  haloalkyl;   m and n are each independently 0 or an integer of 1, 2 or 3;   Q is ##STR7## X is NR 4  or S; R 1  is H, halogen, C 1  -C 8  alkyl, or C 2  -C 8  alkenyl;   R 2  and R 3  are each independently H, C 1  -C 8  alkyl, C 1  -C 8  haloalkyl, C 1  -C 8  alkoxy, C 1  -C 8  haloalkoxy, halogen, CN, NO 2 , COR 5  or phenyl optionally substituted with one to three halogen or NR 6  R 7  groups or R 1  and R 2  may be taken together with the atoms to which they are attached to form a saturated or unsaturated 6-membered carbocyclic ring optionally substituted with one to three halogen, NO 2 , C 1  -C 4  alkyl or C 1  -C 4  alkoxy groups;   R 4  is C 1  -C 8  alkyl, C 2  -C 8  alkenyl or phenyl; and   R 5 , R 6  and R 7  are each independently H or C 1  -C 4  alkyl.   
     
     
       2. The method according to claim 1 wherein m and n are 0. 
     
     
       3. The method according to claim 1 wherein R is C 1  -C 4  alkyl or C 2  -C 4  alkenyl. 
     
     
       4. The method according to claim 1 wherein Q is ##STR8## . 
     
     
       5. The method according to claim 1 wherein Q is ##STR9## . 
     
     
       6. The method according to claim 1 wherein the fouling organism is selected from the group consisting of barnacles, zebra mussels, algae, diatoms, hydroids, bryozoa, ascidians, tubeworms and Asiatic clams. 
     
     
       7. The method according to claim 4 wherein the formula I compound is selected from the group consisting of (3-vinylimidazolinio)vinyldiphenylboron, (3-vinylimidazolinio)methyldiphenylboron, (3-isopropylimidazolinio)vinyldiphenylboron, and (thiazolinio)methyldiphenylboron. 
     
     
       8. The method according to claim 5 wherein the formula I compound is selected from the group consisting of (3-methylpyridinio)methyldiphenylboron, (4-phenylpyridinio)methyldiphenylboron, (4-t-butylpyridinio)methyldiphenylboron, (4-isopropylpyridinio)methyldiphenylboron, (3-bromopyridinio)methyldiphenylboron, (4-acetylpyridinio)methyldiphenylboron, (4-cyanopyridinio)methyldiphenylboron, (isoquinolinio)methyldiphenylboron, (3-bromoisoquinolinio)methyldiphenylboron and (5,6,7,8-tetrahydroisoquinolinio)methyldiphenylboron). 
     
     
       9. A method for protecting an aquatic structure against fouling by a marine or freshwater fouling organism which comprises applying onto or permeating into said structure an antifouling-effective amount of a compound of formula I ##STR10## wherein R is C 1  -C 8  alkyl, C 2  -C 8  alkenyl or C 2  -C 8  alkynyl; W and Y are each independently halogen, C 1  -C 8  alkyl or C 1  -C 8  haloalkyl;   m and n are each independently 0 or an integer of 1, 2 or 3;   Q is ##STR11## X is NR 4  or S; R 1  is H, halogen, C 1  -C 8  alkyl, or C 2  -C 8  alkenyl;   R 2  and R 3  are each independently H, C 1  -C 8  alkyl, C 1  -C 8  haloalkyl, C 1  -C 8  alkoxy, C 1  -C 8  haloalkoxy, halogen, CN, NO 2 , COR 5  or phenyl optionally substituted with one to three halogen or NR 6  R 7  groups or R 1  and R 2  may be taken together with the atoms to which they are attached to form a saturated or unsaturated 6-membered carbocyclic ring optionally substituted with one to three halogen, NO 2 , C 1  -C 4  alkyl or C 1  -C 4  alkoxy groups;   R 4  is C 1  -C 8  alkyl, C 2  -C 8  alkenyl or phenyl; and   R 5 , R 6  and R 7  are each independently H or C 1  -C 4  alkyl.   
     
     
       10. The method according to claim 9 wherein m and n are 0. 
     
     
       11. The method according to claim 9 wherein R is C 1  -C 4  alkyl or C 2  -C 4  alkenyl. 
     
     
       12. The method according to claim 9 wherein the aquatic structure is a fishnet, boat, ship, piling, pier, intake screen, cooling tower, pipeline or standpipe. 
     
     
       13. The method according to claim 9 wherein the marine or freshwater fouling organism is selected from the group consisting of barnacles, zebra mussels, algae, diatoms, hydroids, bryozoa, ascidians, tubeworms and Asiatic clams. 
     
     
       14. The method according to claim 11 wherein the formula I compound is selected from the group consisting of (3-vinylimidazolinio)vinyldiphenylboron, (3-vinylimidazolinio)methyldiphenylboron, (3-methylpyridinio)methyldiphenylboron, (4-phenylpyridinio)methyldiphenylboron, (4-t-butylpyridinio)methyldiphenylboron, (4-isopropylpyridinio)methyldiphenylboron, (3-isopropylimidazolinio)vinyldiphenylboron, (thiazolinio)methyldiphenylboron, (3-bromopyridinio)methyldiphenylboron, (4-acetylpyridinio)methyldiphenylboron, (4-cyanopyridinio)methyldiphenylboron, (isoquinolinio)methyldiphenylboron, (3-bromoisoquinolinio)methyldiphenylboron and 5,6,7,8-tetrahydroisoquinolinio)methyldiphenylboron.